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Flufenamic Acid
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WARNING: This product is for research use only, not for human or veterinary use.

Hodoodo CAT#: H328901

CAS#: 530-78-9

Description: Flufenamic Acid (also known as CI-440, CN-27554, and INF-1837) is a cyclooxygenase inhibitor used to treat inflammation and pain.

Chemical Structure

Flufenamic Acid

CAS# 530-78-9

Instruction

Theoretical Analysis

Hodoodo Cat#: H328901
Name: Flufenamic Acid
CAS#: 530-78-9
Chemical Formula: C14H10F3NO2
Exact Mass: 281.07
Molecular Weight: 281.234
Elemental Analysis: C, 59.79; H, 3.58; F, 20.27; N, 4.98; O, 11.38

Price and Availability

Size	Price	Availability
10g	USD 250	2 Weeks
25g	USD 450	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. Hodoodo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Flufenamic Acid; CI-440; CN-27554; INF-1837; CI 440; CN 27554; INF 1837; CI440; CN27554; INF1837

IUPAC/Chemical Name: 2-((3-(trifluoromethyl)phenyl)amino)benzoic acid

InChi Key: LPEPZBJOKDYZAD-UHFFFAOYSA-N

InChi Code: InChI=1S/C14H10F3NO2/c15-14(16,17)9-4-3-5-10(8-9)18-12-7-2-1-6-11(12)13(19)20/h1-8,18H,(H,19,20)

SMILES Code: O=C(O)C1=CC=CC=C1NC2=CC=CC(C(F)(F)F)=C2

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Instruction:

View handling instruction

Biological target:	Flufenamic acid is a non-steroidal anti-inflammatory agent, inhibits cyclooxygenase (COX), activates AMPK, and also modulates ion channels, blocking chloride channels and L-type Ca2+ channels, modulating non-selective cation channels (NSC), activating K+ channels.
In vitro activity:	Oil red O staining and quantification indicated that 12.5, 25, 50, 100, and 200 μM FFA (flufenamic acid) had an inhibitory effect on the adipogenic differentiation of hASCs cultured in AM on day 21 (Figures 1(a) and 1(b)). Meanwhile, qRT-PCR showed that 12.5, 25, 50, and 100 μM FFA significantly attenuated the expression of PPARG (Figure 1(c)) and CEBPA (Figure 1(d)) at day 14, whereas FFA at 200 μM did not. Reference: Stem Cells Int. 2020; 2020: 1540905. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7102471/
In vivo activity:	The inflammatory response was obviously enhanced in CLP-constructed sepsis rats and alleviated by FFA (flufenamic acid) treatment. Sepsis induced the increase of W/D ratio, promoted the levels of TNF-α, IL-6, HMGBR1, and MDA and inhibited the levels of SOD and GSH. FFA could effectively alleviate the sepsis-induced lung injury. Reference: Drug Dev Res. 2020 Nov;81(7):885-892. https://pubmed.ncbi.nlm.nih.gov/32542754/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	59.0	209.79
	Ethanol	31.7	112.75

Preparing Stock Solutions

The following data is based on the product molecular weight 281.23 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Liu X, Li Z, Liu H, Zhu Y, Xia D, Wang S, Gu R, Zhang P, Liu Y, Zhou Y. Flufenamic Acid Inhibits Adipogenic Differentiation of Mesenchymal Stem Cells by Antagonizing the PI3K/AKT Signaling Pathway. Stem Cells Int. 2020 Mar 16;2020:1540905. doi: 10.1155/2020/1540905. PMID: 32256607; PMCID: PMC7102471. 2. Ge R, Hu L, Tai Y, Xue F, Yuan L, Wei G, Wang Y. Flufenamic acid promotes angiogenesis through AMPK activation. Int J Oncol. 2013 Jun;42(6):1945-50. doi: 10.3892/ijo.2013.1891. Epub 2013 Apr 10. PMID: 23589027. 3. Jiang Q, Chen Z, Jiang H. Flufenamic acid alleviates sepsis-induced lung injury by up-regulating CBR1. Drug Dev Res. 2020 Nov;81(7):885-892. doi: 10.1002/ddr.21706. Epub 2020 Jun 16. PMID: 32542754. 4. Zhang S, Huo S, Li H, Tang H, Nie B, Qu X, Yue B. Flufenamic acid inhibits osteoclast formation and bone resorption and act against estrogen-dependent bone loss in mice. Int Immunopharmacol. 2020 Jan;78:106014. doi: 10.1016/j.intimp.2019.106014. Epub 2019 Nov 24. PMID: 31776093.
In vitro protocol:	1. Liu X, Li Z, Liu H, Zhu Y, Xia D, Wang S, Gu R, Zhang P, Liu Y, Zhou Y. Flufenamic Acid Inhibits Adipogenic Differentiation of Mesenchymal Stem Cells by Antagonizing the PI3K/AKT Signaling Pathway. Stem Cells Int. 2020 Mar 16;2020:1540905. doi: 10.1155/2020/1540905. PMID: 32256607; PMCID: PMC7102471. 2. Ge R, Hu L, Tai Y, Xue F, Yuan L, Wei G, Wang Y. Flufenamic acid promotes angiogenesis through AMPK activation. Int J Oncol. 2013 Jun;42(6):1945-50. doi: 10.3892/ijo.2013.1891. Epub 2013 Apr 10. PMID: 23589027.
In vivo protocol:	1. Jiang Q, Chen Z, Jiang H. Flufenamic acid alleviates sepsis-induced lung injury by up-regulating CBR1. Drug Dev Res. 2020 Nov;81(7):885-892. doi: 10.1002/ddr.21706. Epub 2020 Jun 16. PMID: 32542754. 2. Zhang S, Huo S, Li H, Tang H, Nie B, Qu X, Yue B. Flufenamic acid inhibits osteoclast formation and bone resorption and act against estrogen-dependent bone loss in mice. Int Immunopharmacol. 2020 Jan;78:106014. doi: 10.1016/j.intimp.2019.106014. Epub 2019 Nov 24. PMID: 31776093.

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1: Hendriks CM, Penning TM, Zang T, Wiemuth D, Gründer S, Sanhueza IA, Schoenebeck F, Bolm C. Pentafluorosulfanyl-containing flufenamic acid analogs: Syntheses, properties and biological activities. Bioorg Med Chem Lett. 2015 Oct 15;25(20):4437-40. doi: 10.1016/j.bmcl.2015.09.012. Epub 2015 Sep 8. PubMed PMID: 26372652; PubMed Central PMCID: PMC4599580.

2: Hoppel M, Ettl H, Holper E, Valenta C. Influence of the composition of monoacyl phosphatidylcholine based microemulsions on the dermal delivery of flufenamic acid. Int J Pharm. 2014 Nov 20;475(1-2):156-62. doi: 10.1016/j.ijpharm.2014.08.058. Epub 2014 Aug 29. PubMed PMID: 25178824.

3: Mahrhauser DS, Kählig H, Partyka-Jankowska E, Peterlik H, Binder L, Kwizda K, Valenta C. Investigation of microemulsion microstructure and its impact on skin delivery of flufenamic acid. Int J Pharm. 2015 Jul 25;490(1-2):292-7. doi: 10.1016/j.ijpharm.2015.05.056. Epub 2015 May 26. PubMed PMID: 26022888.

4: Hoppel M, Juric S, Ettl H, Valenta C. Effect of monoacyl phosphatidylcholine content on the formation of microemulsions and the dermal delivery of flufenamic acid. Int J Pharm. 2015 Feb 1;479(1):70-6. doi: 10.1016/j.ijpharm.2014.12.048. Epub 2014 Dec 24. PubMed PMID: 25542986.

5: Bencze M, Behuliak M, Vavřínová A, Zicha J. Broad-range TRP channel inhibitors (2-APB, flufenamic acid, SKF-96365) affect differently contraction of resistance and conduit femoral arteries of rat. Eur J Pharmacol. 2015 Oct 15;765:533-40. doi: 10.1016/j.ejphar.2015.09.014. Epub 2015 Sep 16. PubMed PMID: 26384458.

6: Delaney SP, Korter TM. Terahertz spectroscopy and computational investigation of the flufenamic acid/nicotinamide cocrystal. J Phys Chem A. 2015 Apr 2;119(13):3269-76. doi: 10.1021/jp5125519. Epub 2015 Mar 23. PubMed PMID: 25787318.

7: Guinamard R, Simard C, Del Negro C. Flufenamic acid as an ion channel modulator. Pharmacol Ther. 2013 May;138(2):272-84. doi: 10.1016/j.pharmthera.2013.01.012. Epub 2013 Jan 25. Review. PubMed PMID: 23356979; PubMed Central PMCID: PMC4116821.

8: Guo M, Wang K, Hamill N, Lorimer K, Li M. Investigating the Influence of Polymers on Supersaturated Flufenamic Acid Cocrystal Solutions. Mol Pharm. 2016 Sep 6;13(9):3292-307. doi: 10.1021/acs.molpharmaceut.6b00612. Epub 2016 Aug 15. PubMed PMID: 27494289.

9: Chavez-Dozal AA, Jahng M, Rane HS, Asare K, Kulkarny VV, Bernardo SM, Lee SA. In vitro analysis of flufenamic acid activity against Candida albicans biofilms. Int J Antimicrob Agents. 2014 Jan;43(1):86-91. doi: 10.1016/j.ijantimicag.2013.08.018. Epub 2013 Oct 1. PubMed PMID: 24156913; PubMed Central PMCID: PMC3902125.

10: Pyatski Y, Zhang Q, Mendelsohn R, Flach CR. Effects of permeation enhancers on flufenamic acid delivery in Ex vivo human skin by confocal Raman microscopy. Int J Pharm. 2016 May 30;505(1-2):319-28. doi: 10.1016/j.ijpharm.2016.04.011. Epub 2016 Apr 6. PubMed PMID: 27063850.

11: Tarushi A, Kastanias P, Raptopoulou CP, Psycharis V, Kessissoglou DP, Papadopoulos AN, Psomas G. Zinc complexes of flufenamic acid: Characterization and biological evaluation. J Inorg Biochem. 2016 Apr 22. pii: S0162-0134(16)30108-8. doi: 10.1016/j.jinorgbio.2016.04.023. [Epub ahead of print] PubMed PMID: 27155725.

12: Malinovskaja-Gomez K, Labouta HI, Schneider M, Hirvonen J, Laaksonen T. Transdermal iontophoresis of flufenamic acid loaded PLGA nanoparticles. Eur J Pharm Sci. 2016 Jun 30;89:154-62. doi: 10.1016/j.ejps.2016.04.034. Epub 2016 Apr 27. PubMed PMID: 27131608.

13: Bal R, Ustundag Y, Bulut F, Demir CF, Bal A. Flufenamic acid prevents behavioral manifestations of salicylate-induced tinnitus in the rat. Arch Med Sci. 2016 Feb 1;12(1):208-15. doi: 10.5114/aoms.2016.57597. Epub 2016 Feb 2. PubMed PMID: 26925138; PubMed Central PMCID: PMC4754382.

14: Monteillier A, Loucif A, Omoto K, Stevens EB, Vicente SL, Saintot PP, Cao L, Pryde DC. Investigation of the structure activity relationship of flufenamic acid derivatives at the human TRESK channel K(2P)18.1. Bioorg Med Chem Lett. 2016 Oct 15;26(20):4919-4924. doi: 10.1016/j.bmcl.2016.09.020. PubMed PMID: 27641472.

15: Tolia C, Papadopoulos AN, Raptopoulou CP, Psycharis V, Garino C, Salassa L, Psomas G. Copper(II) interacting with the non-steroidal antiinflammatory drug flufenamic acid: structure, antioxidant activity and binding to DNA and albumins. J Inorg Biochem. 2013 Jun;123:53-65. doi: 10.1016/j.jinorgbio.2013.02.009. Epub 2013 Feb 28. PubMed PMID: 23528572.